$225,000
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533 Round Top RD, Chestertown, MD 21620

4 Beds
2 Baths
1,800 Sq Ft

Introducing this spacious 4-bedroom, 1.5-bath ranch on an extra-wide fenced lot in the Chester Harbor community, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan ready for your personal updates and vision. Whether youre looking for your next home, an investment opportunity, or a property to renovate and build equity, this home offers exceptional potential. The generous layout includes four bedrooms, one full bath, one half bath, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, youll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying life on the water. Ideally located near marinas, parks, and the shops, restaurants, and waterfront charm of historic downtown Chestertown, this property offers the perfect blend of space, convenience, recreation, and opportunity. Priced to reflect its condition, this is a chance to create a home thats uniquely your own while building equity in a sought-after location.

  • MLS# MDQA2018038
  • Date Listed07/19/2026
  • Days on Realty 28 Days
  • Bedrooms 4
  • Bathrooms 1 Full baths, 1 Half baths
  • Lot Size 0.55 acres (24,000 sq. ft)
  • Subdivision CHESTER HARBOR
  • Year Built 1962
  • Square Feet 1,800 sq. ft
  • Price Per Sq. Ft $125

Interior Features

  • Cooling None
  • Heating Forced Air

Exterior / Lot Features

  • Roof -
  • Lot Size Acres 0.55
  • Lot Size SQFT 24,000.00
  • Lot Features -

Financial Considerations

  • Tax Amount $2,144
  • Terms Cash, Conventional, FHA, VA Loan

Schools near 21620

Explore the local neighborhood highlights and top-rated schools near 21620 in Chestertown, MD.

Nearby Schools

Source: School Digger

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for 21620

Discover key demographics, population statistics, and environmental insights for the Chestertown, MD area.

Population & Environment

Source: Sperling's Best Places

Walkability in MD / 21620

Source: Walk Score

1/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

29/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.


Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 8/100, Transit Score: 0/100, Bike Score: 28/100.

Property Change History

Property description updated with new details

Frequently Asked Questions for 533 Round Top Rd

Source: Realty.com

533 Round Top Rd, Chestertown, MD 21620 in CHESTER HARBOR, Chestertown, MD 21620 is a single family listed at $225,000. Highlights include 4 bedrooms, 2 bathrooms, 1,800 sq. ft., built in 1962, 0.55 acre lot, $125 per sq. ft.. Realty.com has 1 photos, sales history, school insights, and mortgage tools for this listing.

Our records indicate that 533 Round Top Rd was built in 1962.

The full address for this home is 533 Round Top Rd, Chestertown, MD 21620.

533 Round Top Rd has been listed on Realty.com since Sun July 19, 2026

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 8/100, Transit Score: 0/100, Bike Score: 28/100.

There are 3 schools assigned to this home. Check out the schools near 533 Round Top Rd. Grasonville Elementary School (Grades: PK - 5), Kennard Elementary School (Grades: 3 - 5), Queen Anne's County High School (Grades: 9 - 12)

Listing provided courtesy of: Exp Realty, Llc (tel: 833-335-7433)
Listing agent: Christopher Craddock (tel: 703-995-0333) (#3049573)

This content last refreshed on 2026-08-16 22:06:13. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.